JPH095989A - Pigment-dispersed composition, forming method of color image using the composition, and color image - Google Patents

Abstract

PURPOSE: To provide a pigment-dispersed material having excellent coloring property and adaptability for use, especially having excellent properties against aggregation and crystallization and excellent fluidity in which the pigment particles are dispersed in a very fine state by incorporating an org. pigment and an alkanolamine as a dispersant for this org. pigment. CONSTITUTION: The compsn. contains at least an org. pigment and an alkanolamine as a dispersant for this org. pigment. The alkanolamine which acts as the dispersant for the pigment is preferably an alkanolamine containing two or more nitrogen atoms in the molecule. This alkanolamine may be used as a single material, or two or more alkanolamines may be used together. Or, another dispersant may be used with the alkanolamine together. In this case, examples of alkanolamines are monoethanolamines and diethanolamines, and more preferably, N,N,N',N'-tetra(hydroxyethyl)-1,2-diaminoethane, N,N,N'-tri(hydroxyethyl)-1,2-diaminoethane and the like are used.

Description

Detailed Description of the Invention

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a pigment dispersion composition having excellent suitability for use, particularly non-aggregation property, non-crystallinity, fluidity and coloring power. The pigment dispersion composition according to the present invention,
It is preferably used for the formation of multicolored colored images on substrates such as paints, printing inks, color display plates using them, or color proofs, and especially for manufacturing color filters used for liquid crystal color displays and the like.

[0002]

2. Description of the Related Art Generally, a practically useful pigment that exhibits a vivid color tone and high tinting strength is composed of fine particles. However, when the pigment particles are further miniaturized in order to obtain high tinting strength, the pigment dispersion often exhibits high viscosity, which makes it difficult to take out the dispersion from the disperser and transport it through a pipeline. In some cases, gelation occurs during storage, which makes it difficult to use.

[0003] A colored photosensitive composition containing a pigment as a coloring agent is useful as an image forming material and is used in various fields. As described above, the pigment is required to have a clear color tone and high tinting strength, but when used as a photosensitive composition, the following problems occur and it is difficult to make the pigment fine.

[0004] In order to form a colored image using the colored photosensitive composition, a layer of the photosensitive composition is formed on a substrate, exposed, and exposed.
develop. At this time, as a developer, an alkaline aqueous solution is preferably used rather than an organic solvent from an environmental problem. Therefore, the colored layer is required to be soluble in the alkaline aqueous solution. Further, from the viewpoint of drying after coating, it is preferable to use an organic solvent as a dispersion medium for the coating solution of the colored photosensitive composition, and the binder (binder) used in the colored photosensitive composition is preferably an acidic group. And must be soluble in a suitable organic solvent. Organic pigments are dispersed in such an acidic binder.

However, it is difficult to disperse an organic pigment in an acidic binder that is soluble in an organic solvent, and the pigment is sufficiently finely divided, has high coloring power, and can be developed with an alkaline aqueous solution. It was difficult to obtain a hydrophilic composition.

As one of the fields of application of the pigment dispersion composition,
There are color filters used for liquid crystal displays and the like.
The color filter is formed by disposing a coloring material in each pixel portion so that the three primary colors of red, green, and blue are selectively transmitted. Various methods are known for disposing the coloring material in the pixel portion, and a dyeing method, a printing method, an electrodeposition method, a pigment dispersion method and the like have been put into practical use. Among these, the pigment dispersion method is excellent in terms of the quality of the obtained color filter and the stability of the production process.

In the pigment dispersion method, a colored photosensitive composition solution containing a pigment dispersion composition is provided on a transparent substrate, pattern-exposed and then developed to form a pixel pattern of the first color,
By repeating this a plurality of times, pixel patterns of a plurality of colors are formed on the substrate. Since a pigment is used as a coloring material, if the pigment is not sufficiently miniaturized, light is scattered and absorbed by the pigment particles, and the light transmittance is reduced. Furthermore, the polarization axis is rotated by the scattering of light and birefringence due to the pigment particles, and the contrast of the liquid crystal display device is also reduced (1990 7th color optical conference 512 color display 10.4 "size TFT-LCD use. (Color filters: Ueki, Koseki, Fukunaga, Yamanaka.) Therefore, further miniaturization of pigment particles is required.

In order to solve the above various problems,
Many proposals have been made so far in order to produce a pigment dispersion having a sufficient fluidity and a fine particle size.
The contents can be broadly divided into two categories according to the technical method.

One is to use an organic pigment as a base skeleton, and a side chain of which is a sulfone group, a sulfonamide group, an aminomethyl group,
In this method, a pigment derivative obtained by introducing a substituent such as a phthalimidomethyl group is mixed to coat the surface of the pigment (Japanese Patent Publication No. 41-2466). As a specific example, British Patent No. 94
9739, U.S. Pat. No. 4,313,766, Japanese Patent Publication No. 39
Nos. 2884 and 57-12067 disclose phthalocyanine derivatives effective for dispersing phthalocyanine pigments. However, in order to use these pigment derivatives as a dispersant, it is necessary that the pigments to be treated with the pigments have the same color tone or similar skeleton, and the applicable pigments are extremely limited.

The other is a method of coating the pigment surface with a substantially colorless compound. Various compounds have been proposed so far, but as a compound having versatility as a dispersant, Japanese Patent Publication No. 54-34009 and British Patent No. 1342 have been proposed.
The specification of No. 746 describes a compound comprising a terminal carboxyl group-containing polyester obtained by dehydrating a hydroxycarboxylic acid or a salt thereof. Japanese Patent Laid-Open No. Hei 2
No. 245231 discloses that a product obtained by esterifying tetrakis (2-hydroxyalkyl) ethylenediamine with a hydroxyl group-containing and non-containing higher monocarboxylic acid is subjected to ring-opening addition of a higher monocarboxylic acid glycidyl ester, and then an acidic group, A polymer dispersant composed of a modified polyester type compound obtained by introducing a basic group or both is described. However, even with the use of these polymer dispersants, it was difficult to achieve both sufficient fluidity to solve the above problems and miniaturization of pigment particles.

On the other hand, as an example of a low molecular weight dispersant, US Pat. No. 3,536,510 discloses the use of an alkanolamine compound for dispersing titanium oxide in an aqueous medium. However, there was no finding of an application example to the dispersion of the organic pigment in the non-aqueous system.

[0012]

SUMMARY OF THE INVENTION An object of the present invention is to provide a pigment dispersion having excellent suitability for use, particularly non-aggregating property, non-crystallinity, fluidity, fine pigment particles, and excellent coloring power, and the same. And has aptitude for development with an alkaline aqueous solution,
Another object is to provide a colored image having high coloring power.

[0013]

The object of the present invention has been achieved by a pigment dispersion composition containing at least an organic pigment and an alkanolamine as a dispersant for the organic pigment, and a colored image using the same. Hereinafter, the present invention will be described in detail.

In the present invention, the alkanolamine acting as a dispersant for the pigment is preferably an alkanolamine containing two or more nitrogen atoms in the molecule. Examples of these include compounds represented by formula (1), formula (2) or formula (3).

[0015]

Embedded image

R in equation (1)₁~ R_FourAt least one of
Hydroxyalkyl group, hydroxyalkyleneoxya
Alkyl group, hydroxypolyalkyleneoxyalkyl group
It is. The term hydroxyalkyl group, hydroxy
Alkyleneoxyalkyl group, hydroxypolyalkyl
As an oxyalkyl group,-(CH₂CH₂O) n-
H (n is 1 to 40),-(CH₂CHCH_ThreeO) m-H
(M is 1 to 40),-(CH₂CH₂O) n- (CH₂CH
CH_ThreeO) m-H (n + m is 2 to 40),-(CH ₂CH
CH_ThreeO) n- (CH₂CH₂O) m-H (n + m is 2-4)
0),-(CHR₆) X-OH (x is 1 to 40)
It is. R₆Is a hydrogen atom or a lower group which may have a substituent
It is an alkyl group. As a substituent, an alkoxy group, hydr
Roxy group. Remaining R₁~ R_FourIs a hydrogen atom or substitution
It is an alkyl group which may have a group. As a substituent
Rucoxy group and hydroxy group. R₁~ R_FourTwo of
The above are hydroxyalkyl groups and hydroxyalkylene groups.
Xyalkyl group, hydroxypolyalkyleneoxyal
When they are kill groups, they may be the same or different.
May be. R_FiveHas a hydrogen atom or a substituent
It is a good lower alkyl group. Alkoxy as a substituent
Group, a hydroxy group. A in the formula (1) is 1 to 20
It is an integer.

R in equation (2)₇~ R_TenAt least one of
Is a hydroxyalkyl group, hydroxyalkyleneoxy
Alkyl group, hydroxypolyalkyleneoxyalkyl
Group. Hydroxyalkyl group, hydroxy here
Sialkylene oxyalkyl group, hydroxypolyalkyl
As a renoxyalkyl group,-(CH₂CH₂O) n
-H (n is 1 to 40),-(CH₂CHCH_ThreeO) m-H
(M is 1 to 40),-(CH₂CH₂O) n- (CH₂CH
CH_ThreeO) m-H (n + m is 2 to 40),-(CH ₂CH
CH_ThreeO) n- (CH₂CH₂O) m-H (n + m is 2-4)
0),-(CHR₁₂) X-OH (x is 1 to 40)
Can be R₁₂May have a hydrogen atom or a substituent
It is a primary alkyl group. As a substituent, an alkoxy group,
It is a droxy group. Remaining R₇~ R_TenIs a hydrogen atom or
It is an alkyl group which may have a substituent. As a substituent
Is an alkoxy group or a hydroxy group. R₇~ R_TenHorse
2 or more are hydroxyalkyl groups, hydroxyalky
Renoxyalkyl group, hydroxypolyalkylene
When they are sialkyl groups, they may be the same,
It may be different. R₁₁Has a hydrogen atom or a substituent
It may be a lower alkyl group. As a substituent
It is a Coxy group and a hydroxy group. In the formula (2), b is 1 to
It is an integer of 3.

R in equation (3)₁₃, R₁₄At least one of
Is a hydroxyalkyl group, hydroxyalkyleneoxy
Alkyl group, hydroxypolyalkyleneoxyalkyl
Group. Hydroxyalkyl group, hydroxy here
Sialkylene oxyalkyl group, hydroxypolyalkyl
As a renoxyalkyl group,-(CH₂CH₂O) n
-H (n is 1 to 40),-(CH₂CHCH_ThreeO) m-H
(M is 1 to 40),-(CH₂CH₂O) n- (CH₂CH
CH_ThreeO) m-H (n + m is 2 to 40),-(CH ₂CH
CH_ThreeO) n- (CH₂CH₂O) m-H (n + m is 2-4)
0),-(CHR_Fifteen) X-OH (x is 1 to 40)
Can be R_FifteenMay have a hydrogen atom or a substituent
It is a primary alkyl group. As a substituent, an alkoxy group,
It is a droxy group. Remaining R₁₃, R₁₄Is a hydrogen atom or
It is an alkyl group which may have a substituent. As a substituent
Is an alkoxy group or a hydroxy group. R₁₃, R₁₄Both
Hydroxyalkyl group, hydroxyalkylene
Cyalkyl group, hydroxypolyalkyleneoxy alk
When it is a group, it may be the same or different.
May be. R₁₆~ R₁₉Has a hydrogen atom or a substituent
It may be a lower alkyl group. Alcohol as a substituent
A xy group and a hydroxy group.

A compound containing one nitrogen atom in the molecule can also be used. Examples include compounds represented by formula (4).

[0020]

Embedded image

In the formula, at least one of R _{20 to} R ₂₂ is a hydroxyalkyl group, a hydroxyalkyleneoxyalkyl group or a hydroxypolyalkyleneoxyalkyl group. Hydroxyalkyl groups referred to herein, hydroxy alkyleneoxy alkyl group, the hydroxy polyalkyleneoxy alkyl _{group, - (CH 2 CH 2 O} ) n-H
(N is _{1~40), - (CH 2 CHCH} 3 O) m-H (m
Is _{1~40), - (CH 2 CH} 2 O) n- (CH 2 CHCH
_{3 O) m-H (n} + m is _{2~40), - (CH 2 CHCH} 3
_{O) n- (CH 2 CH 2} O) m-H (n + m is 2 to 40),
_{- (CHR 23) x-OH} (x is 1 to 40) are exemplified. R ₂₃ is a hydrogen atom or a lower alkyl group which may have a substituent. Examples of the substituent include an alkoxy group and a hydroxy group. The remaining R _{20 to} R ₂₂ are a hydrogen atom or an alkyl group which may have a substituent. Examples of the substituent include an alkoxy group and a hydroxy group. When two or more of R _{20 to} R ₂₂ are a hydroxyalkyl group, a hydroxyalkyleneoxyalkyl group or a hydroxypolyalkyleneoxyalkyl group, each may be the same,
It may be different.

As the dispersant, the above alkanolamines may be used alone or in combination. 2 in the molecule
When an alkanolamine containing one or more nitrogen atoms and an alkanolamine containing one nitrogen atom in the molecule are used in combination, the ratio of the former is 5% or more, preferably 50% or more in a mixture of both. .

Further, the above alkanolamine may be used in combination with another dispersant. In this case, it is advantageous to use the alkanolamine in an amount of 5% or more, preferably 50% or more.

Specific examples of preferable alkanolamines include monoethanolamine, diethanolamine, triethanolamine, hydroxyethylpolyoxyethyleneoxyethyldimethylamine, hydroxyethylpolyoxyethyleneoxyethyldiethylamine, hydroxypropylpolyoxypropyleneoxyethyldimethylamine. Hydroxypropyl polyoxypropylene oxyethyl diethylamine, hydroxypropyl polyoxypropylene polyoxyethylene oxyethyl dimethylamine, hydroxypropyl polyoxypropylene polyoxyethylene oxyethyl diethylamine,

More preferably, N, N, N ', N'-tetra (hydroxyethyl) -1,2-diaminoethane,
N, N, N'-tri (hydroxyethyl) -1,2-diaminoethane, N, N'-di (hydroxyethyl)-
1,2-diaminoethane, N, N-di (hydroxyethyl) -1,2-diaminoethane, hydroxyethyl-
1,2-diaminoethane, N, N, N ′, N′-tetra (hydroxyethylpolyoxyethylene) -1,2-diaminoethane, N, N, N′-tri (hydroxyethylpolyoxyethylene) -1 , 2-diaminoethane, N,
N-di (hydroxyethylpolyoxyethylene) -1,
2-diaminoethane, N, N'-di (hydroxyethylpolyoxyethylene) -1,2-diaminoethane, hydroxyethylpolyoxyethylene-1,2-diaminoethane, 1- (2-hydroxyethyl) piperazine,
1,4 bis (2-hydroxyethyl) piperazine and the like can be mentioned.

The ratio of the dispersant in the pigment dispersion composition is 0.1 to 200 parts by weight based on 100 parts by weight of the pigment.
Preferably, it is used in an amount of 1 to 50 parts by weight.

A solvent is used for dispersing the pigment, and the pigment content in this dispersion is 5 to 80% by weight, preferably 10 to 70% by weight.

Specific examples of organic pigments useful in the present invention are shown below. CI Pigment Yellow 20, CI Pigment Yellow 24, CI Pigment Yellow 83, CI Pigment Yellow 86, CI as a yellow pigment
Pigment Yellow 93, CI Pigment Yellow 109, CI Pigment Yellow 11
0, CI pigment yellow 117, CI pigment yellow 125, CI pigment yellow 137, CI pigment yellow 138, CI pigment yellow 139, C.
I. Pigment yellow 185, CI pigment yellow 147, CI pigment yellow 148, CI pigment yellow 153, CI pigment yellow, CI pigment yellow 154, CI pigment yellow 166, CI pigment yellow 168,

CI pigment orange 36 as an orange pigment,
CI increase range 43, CI increase range 51, CI increase range 55, CI increase range 59, CI increase range 61,

As the red pigment, CI pigment let 9, CI pigment let 97, CI pigment let 122, CI pigment let 123,
CI pagelet 149, CI pagelet 168, CI pagelet 177, CI pagelet 180, CI pagelet 192, CI pagelet 215, CI pagelet 216, CI pagelet 216, CI pagelet 21
7, CI pagelet 220, CI pagelet 223, CI pagelet 224, CI pagelet 226, CI pagelet 227, C.
I. Pigmentlet 228, CI Pigmentlet 240, CI Pigmentlet 48: 1,

As the violet pigment, CI pigment violet 19, CI pigment violet 23, CI pigment violet 29, C.
I. pigment violet 30, CI pigment violet 37, CI pigment violet 40, CI pigment violet 50,

As the blue pigment, CI pigment blue 15, CI pigment blue 15: 6, CI pigment blue 22, CI pigment blue 60,
CI Pigment Blue 64,

As a green pigment, CI pigment green 7, CI pigment green 36,

CI pigment black 23 as a brown pigment,
CI Pigment Brown 25, CI Pigment Brown 26,

Examples of the black pigment include CI pigment black 7 and the like.

Preferably, the pigment yellow 139 and the pigment yellow 1
85 and pigment yellow 83, and particularly preferably pigment yellow 13
Is 9.

Examples of the method for producing a pigment dispersion composition using the pigment dispersant according to the present invention include the following methods.
The desired effect can be obtained by either method.

1. The pigment composition obtained by previously mixing the pigment and the pigment dispersant is added to the vehicle and dispersed. 2. The pigment and the pigment dispersant are separately added to the vehicle and dispersed. 3. The pigment and the pigment dispersant are separately dispersed in a vehicle in advance, and the resulting dispersion is mixed. In this case, the pigment dispersant may be dispersed only with the solvent. 4. After dispersing the pigment in the vehicle, the pigment dispersant is added to the resulting dispersion. Here, the vehicle means that when the paint is in a liquid state,
It refers to the part of the medium in which the pigment is dispersed, and is composed of a component that is liquid and that binds the pigment to solidify the coating film (binder) and a component that dissolves and dilutes this (solvent).

As a method for adjusting the pigment dispersion composition of the present invention, the pigment can be well dispersed by using various dispersing machines such as a kneader, a roll mill, an attritor, a super mill, a dissolver, a homomixer and a sand mill. .

To form a colored image using the above-mentioned pigment dispersion composition, a pigment dispersion composition liquid is applied on a support and dried to form a layer, or the composition formed on a temporary support. There is a method in which the above layer is transferred, a publicly known positive type or negative type photosensitive resin composition is provided thereon, and the layer is exposed and developed.

When the colored photosensitive composition is used, the pigment dispersion composition and the photosensitive composition are mixed. The material of the photosensitive composition according to the present invention is known, for example, JP-A-3-
All of the photosensitive compositions described in 282404 can be used. Specific examples include a photosensitive composition comprising a negative-type diazo resin and a binder, a photopolymerizable composition, a photosensitive composition comprising an azide compound and a binder, and a cinnamic acid-type photosensitive composition.

Among them, the photopolymerizable composition is particularly preferable. The photopolymerizable composition contains a photopolymerization initiator, a polyfunctional monomer and a binder as basic components.
Further, as the photosensitive composition, those which can be developed with an aqueous alkali solution and those which can be developed with an organic solvent are known, but those which can be developed with an aqueous alkali solution are preferable from the viewpoint of preventing pollution and ensuring labor stability. .

The binder used in the colored photosensitive composition is required to have both the dispersibility of the pigment and the ability to impart alkali developability for use as a photosensitive composition. Specifically, compounds selected from the following wide variety of polymer substances can be used in combination. As the compound that can be combined, the pigment dispersibility is good, the compatibility with the polyfunctional monomer and the photopolymerization initiator is good, and the alkali developer solubility, the organic solvent solubility, the strength, the softening temperature, etc. are suitable. Some are preferred.

Specific examples thereof include copolymers of (meth) acrylic acid and (meth) acrylic acid ester, styrene / maleic anhydride copolymers, and reaction products of the copolymers with alcohols. . Preferably, a copolymer of (meth) acrylic acid and (meth) acrylic acid ester is used. The molecular weight is preferably 5,000 to 200,000. The preferred amount of binders that can be used in combination is such that the total amount of binders is 20 based on total solids.
To 80% by weight.

Solvents for dispersing the pigment preferably used in the present invention include ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, propylene glycol monoethyl ether, diethylene glycol monomethyl ether, ethylene glycol monoethyl ether. Alkylene glycol monoalkyl ethers such as polyalkylene glycol monoalkyl ethers, and acetic acid esters thereof, ethyl acetate, n-propyl acetate,
Acetic acid esters such as i-propyl acetate, n-butyl acetate and i-butyl acetate, aromatic hydrocarbons such as benzene, toluene and xylene, methyl ethyl ketone, acetone,
Examples thereof include ketones such as methyl isobutyl ketone and cyclohexanone, alcohols such as ethanol, propanol, butanol, hexanol, cyclohexanol, ethylene glycol, diethylene glycol and glycerin. Particularly preferred are alkylene glycol monoalkyl ethers and their acetic acid esters, acetic acid esters, and methyl ethyl ketone. The preferred amount of solvent is from 50 to 2000, based on total solids.
% By weight.

Examples of the polyfunctional monomer used in the colored photosensitive composition include known (meth) acrylic acid esters, urethane (meth) acrylates, and (meth) acrylates described in JP-A-60-258539. ) Acrylic amides, allyl compounds, vinyl esters and the like. Preferably, (meth) acrylic acid esters are used. The amount of the monomer is preferably 10 to 60% by weight based on the solid content of the colored photosensitive composition.

The photopolymerization initiator used in the colored photosensitive composition preferably contains at least one component having a molecular extinction coefficient of at least about 50 in the range of about 300 to 500 nm. For example, JP-A-2-486
64, JP-A-1-152449, JP-A-2-153353, aromatic ketones, lophine dimers, benzoin, benzoin ethers, polyhalogens, and There are combinations of two or more of these. Preferably, a combination of 4,4'-bis (diethylamino) benzophenone and 2- (o-chlorophenyl) -4,5-diphenylimidazole dimer, 4- [p-N, N-di (ethoxycarbonylmethyl)- 2,6-di (trichloromethyl) -s-
Triazine]. The content of the photopolymerization initiator is preferably 0.2 to 10% by weight based on the solid content of the photosensitive composition.

When a colored image is prepared using the colored photosensitive composition of the present invention, at least the following steps (1) to (3) are included.

(1) The dispersant according to the present invention, an organic pigment, an alkali-soluble binder and an organic solvent are mixed and sufficiently kneaded to prepare a pigment dispersion, and then a monomer, a photopolymerization initiator and, if necessary, a diluting solvent are added. A step of preparing a colored photosensitive composition by adding,

(2) The obtained colored photosensitive composition is coated on a substrate and dried, or a layer formed by coating on another temporary support is transferred onto the substrate to form a colored photosensitive layer. Forming process,

(3) A step of exposing and developing the colored photosensitive composition layer formed on the substrate to form a pattern.

In the case of a color filter used for a liquid crystal display or the like, the steps (2) and (3) are repeated to form the patterns of the second and subsequent colors in combination. A method of forming a color filter by a transfer method is described in, for example, JP-A-4-208940 and JP-A-5-7272.
Nos. 4, 5-80503, 5-173320, and the like.

A transparent material such as a glass plate or a transparent plastic plate is preferably used as the substrate. In order to improve the adhesion between the substrate and the colored photosensitive composition, various commercially available silane coupling agents or the like may be added to the composition, or the composition may be provided after the composition has been allowed to act on the substrate in advance. .

The method for applying the colored photosensitive composition to the substrate includes spinner, roll coater, bar coater,
A method such as a curtain coater is used.

A suitable method for transferring the composition coated on the temporary support onto the substrate is a method using a heat roll laminator under normal pressure or reduced pressure.

The developer preferably used is an alkali metal or alkaline earth metal hydroxide or carbonate, hydrogen carbonate, aqueous ammonia, quaternary ammonium salt aqueous solution and the like. Particularly preferred is an aqueous solution of sodium carbonate.

Examples of the present invention will be described below.
This does not limit the present application.

[0058]

【Example】

 Example 1 A yellow pigment dispersion having the following formulation was prepared. Pigment Yellow 139 18 g N, N, N ', N'-tetra (hydroxyethyl) 1.1 g-1,2-diaminoethane Methacrylic acid / benzyl methacrylate copolymer 15 g (molar ratio 33/67, weight Average molecular weight 30,000) ・ 1-methoxy-2-propyl acetate 67 g

A motor mill M manufactured by Eiger
At 50, using zirconia beads having a diameter of 0.65 mm,
The mixture was dispersed at a peripheral speed of 9 m / s for 9 hours to prepare a pigment dispersion.

Example 2 N, N, N ', N'-tetra (hydroxyethyl) -1,2-diaminoethane added in Example 1 was mixed with the same weight of 1,4 bis (2-hydroxyethyl). ) A pigment dispersion liquid was prepared in the same manner as in Example 1 except that piperazine was used.

Example 3 N, N, N ′, N′-tetra (hydroxyethyl) -1,2-diaminoethane added in Example 1 was added to N, N having the same weight average molecular weight of 2500. -Hydroxyethyl polyoxyethylene-N ', N'-Hydroxyethyl polyoxyethylene-1,2 diaminoethane was used to prepare a pigment dispersion liquid in the same manner as in Example 1.

Example 4 Example 1 was repeated except that N, N, N ', N'-tetra (hydroxyethyl) -1,2-diaminoethane added in Example 1 was changed to the same weight of diethanolamine. A pigment dispersion was prepared in the same manner as in.

Comparative Example 1 A pigment dispersion liquid was prepared in the same manner as in Example 1 except that the amine was removed from the formulation of Example 1.

The obtained pigment dispersions were compared according to the following evaluation methods. 1. Viscosity measurement: After the obtained pigment dispersion was left standing for 24 hours, the viscosity was measured and evaluated using an E-type viscometer. 2. Contrast measurement: The obtained pigment dispersion liquid was applied on a glass substrate to a film thickness of 6 μm to prepare a sample. This sample was placed between two polarizing plates, the amount of transmitted light when the polarization axes were parallel and when the polarization axes were vertical was measured, and the ratio was defined as the contrast ("1990 7th Color Optical Conference 512 Color Display 10. 4 "size TFT-LCD color filter Ueki, Koseki, Fukunaga, Yamanaka".

Examples 5 to 8 A colored photosensitive composition for a color filter was prepared by the following method, and the contrast was measured. <Preparation of Photopolymerizable Composition> Methacrylic acid / benzyl methacrylate copolymer 30 g (molar ratio 33/67, weight average molecular weight 30,000) Pentaerythritol tetraacrylate 7.7 g 4- [p-N, N -Di (ethoxycarbonylmethyl) 0.3 g-2,6-di (trichloromethyl) -s-triazine] -hydroquinone monomethyl ether 0.01 g-1-methoxy-2-propyl acetate 62 g

As the red pigment, C.I.
I. Pigment Red 177 dispersed in acrylic resin, powder-processed pigment (Color Tech Red U3BN, Sanyo Dye Co., Ltd.) dispersed in 1-methoxy-2-propyl acetate (solid content 33%) 45 g
Then, for color correction, 9 g of each of the yellow pigment dispersions prepared in Examples 1 to 4 were mixed to prepare a red photosensitive composition for a color filter.

Next, the red photosensitive composition for a color filter was applied on a glass substrate with a spinner and dried at 100 ° C. for 2 minutes to form a film of about 2 μm. Then, the film was exposed to an ultra-high pressure mercury lamp under a nitrogen stream, and then developed with a 1% aqueous sodium carbonate solution. The contrast of the obtained sample is
It was measured by the method described above.

Comparative Example 2 A sample was prepared in the same manner as in Example 5 except that the photopolymerizable composition prepared in Example 5 and the pigment dispersion prepared in Comparative Example 1 were used, and the contrast was measured in the same manner. did.

Table 1 shows the evaluation results of the pigment dispersions obtained in Examples and Comparative Examples.

Table 1: Evaluation results ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━ Viscosity (cp) Contrast Pigment dispersion liquid coating Red photosensitivity Composition ───────────────────────────────────── Example 1 75 160 −2 85 150 −3 90 90 −4 130 130 −5 70-1800 6 70-1700 7 70-1700 8 70- 1500 1500 ───────────────────────────── Comparative Example 1 1200 10- 270-150 ━━━━━━━━━━━━━━━━━━━━━━━━━━━━━

From this, it is understood that the pigment dispersion liquid to which the dispersant according to the present invention is added has a low viscosity and a high contrast can be obtained when a color filter is prepared.

[0072]

The pigment dispersion composition according to the present invention is excellent in non-aggregation, non-crystallinity, fluidity, fine pigment particles and excellent coloring power. It is possible to provide a colored image having suitability and high coloring power.

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Claims (7)

[Claims] 1. A pigment dispersion composition comprising at least an organic pigment and an alkanolamine as a dispersant for the organic pigment. 2. The pigment dispersion composition according to claim 1, wherein the alkanolamine contains two or more nitrogen atoms in the molecule. 3. The alkanolamine according to claim 1, wherein the alkanolamine is a mixture of an alkanolamine containing two or more nitrogen atoms in the molecule and an alkanolamine containing one nitrogen atom in the molecule. A pigment dispersion composition. 4. The pigment dispersion composition according to claim 1, claim 2 or claim 3, further comprising an acidic binder. 5. The pigment dispersion composition according to claim 4, which further contains a polyfunctional monomer and a photopolymerization initiator. 6. A method for forming a colored image, which comprises providing the pigment dispersion composition according to claim 5 on a substrate and exposing and developing the composition to form an image. 7. A colored image formed by the method of claim 6.